As a manufacturing method of an aldehyde compound using norbornene compound, for example, methods described in Patent Documents 1 to 3 are known.
Patent Documents 1 to 3 disclose methods for manufacturing formyl cyan norbornene by hydroformylating cyan norbornene using a mixed H2/CO gas in the presence of a catalyst. Patent Documents 1 and 2 disclose an example using a metal compound as a catalyst. Moreover, since it is possible to obtain a target compound with high selectivity, and it is possible to suppress the reaction pressure to be low, a rhodium complex is preferably used as the catalyst.
Patent Document 1 describes that the catalyst may be used at 0.1% by weight to 10% by weight with respect to cyan norbornene. Patent Document 2 describes that with the catalyst concentration of 0.5 mmol/1 to 10 mmol/l, triarylphosphine can be used in a range of 3 moles to 300 moles with respect to 1 mole of rhodium.
Patent Document 4 discloses a method of hydroformylating an olefin-based compound using a mixed H2/CO gas in the presence of a transition metal catalyst and a trivalent phosphorus compound. Furthermore, it is described that as the content of the metal catalyst, a free metal content is 10 ppm to 1,000 ppm based on the weight or volume of the catalyst composition.
Patent Document 5 describes a metal ligand complex catalyst, and exemplifies rhodium as a metal and an organic phosphorus ligand as a ligand. In addition, it is described that the amount of these used, in a case of calculating as a free metal, is a metal concentration in a range of about 1 ppm to 10,000 ppm, and a molar ratio of ligand:metal is 1:1 to 200:1.
In addition, Patent Documents 6 and 7 disclose a method of preparing an aldehyde compound by hydroformylating a linear olefin compound.
In Examples of Patent Document 6, an example of hydroformylating 7-octenal in the presence of a rhodium catalyst and bisphosphite is described. In addition, it is described that about 3 ppmmol, rhodium is used with respect to 1 mole of 7-octenal, and rhodium atoms/phosphorus atoms is 1/20 as a molar ratio. On the other hand, in paragraph 0084 of Patent Document 6, it is described that 2 moles to 1,000 moles in terms of phosphorus atom is preferable with respect to 1 mole of a metal, and in a case of exceeding 1,000 moles, the reaction rate tends to be extremely low.
In addition, Patent Document 7 describes that in the hydroformylation of the olefin, materials such as a halogenated organic compounds are required to be excluded from the reaction, however there is no description regarding the amounts.